094
VOl. 62
NOTES
of the acid, HSbCla, all the compounds listed are included in four different classes: (A) SnC14. 2P, substances ( 5 ) , (12) ; (B) SnC14.P, substances (4), (7), (13); (C) SnCL.P.Solvent, substances (l), ( 2 ) , (3), (8); (D) SbC&.P, substances (6), (10). The chemical nature of the classes A, C and D seems to be clear. They are complex compounds of coordinated hexavalent tin or antimony, one molecule of the phthalein occupying a single coordination valence. The substances of class B may be interpreted by the hypothesis that the phthalein occupies two coordinated valences or they may be considered as bimolecular compounds with two coordination centers. They are mostly less deeply colored and are mainly formed if solvents lacking secondary valences are used. GLASGOW, SCOTLAND
RECEIVED SEPTEMBER 22, 1939
The Condensation of Phenol and Ethylene Oxide BY RICHARD A. SMITH
The monophenyl ether of ethylene glycol was first prepared by the reaction between phenol and ethylene oxide in a sealed tube.' In this way, by heating a t 180' for eight hours, we obtained an 85% yield based on the phenol. More frequently, however, i t has been prepared by the reaction of ethylene chlorohydrin with a phenol salt.2 We find that using this latter method and refluxing the mixture for eight hours gives, after distillation through a 6-foot column and collection within 0.5', 1.10 moles of phenoxy glycol (b. p. 165' a t 80 mrn.), or a 55% yield, from 2 moles of phenol. This same reaction, carried on in a sealed tube for eight hours, gives a 62.5% yield of the same purity. We now find that by heating, without rocking, molar equivalents of phenol and ethylene oxide in an autoclave charged with hydrogen a t tank pressure for four hours until the temperature reaches 200°, the pressure a t that time being in excess of 2500 pounds per sq. in., and then allowing it to cool and redistilling the product in a vacuum, a yield of 94yo of phenoxy glycol of the same purity is obtained. WASHINGTON SQUARECOLLEGE NEWYORKUNIVERSITY WASHINGTON SQUARE,NEWYORKCITY RECEIVED NOVEMBER 24, 1939 (1) Roithner, Monalsh., 76, 6 i 4 (1894). (2) Bentley, Haworth and Perkii+ J. Chcm. Soc., 68, 164 (1896): Smith and Niederl, THISJ O U R N A L , 6S, 808 (1931); Bellman, U.S. P. i , w i , 4 a i ciea2).
